Wolpe has led numerous missions to Israel. The first, in June 2002, was a solidarity mission at the height of the Second Intifada that broke out after the Camp David peace talks. The second, in May 2005, was a mission of gratitude to pick up the Torah commissioned in honor of his recovery from brain surgery.[7] The third, in July 2006, at the height of the 2006 Israel-Hezbollah War, was another solidarity mission that covered Jerusalem, Haifa, and Sderot. In the midst of the second intifada, Wolpe raised three million dollars for victims of terror in a single morning at his synagogue. Wolpe also led the largest American Israel Public Affairs Committee (AIPAC) delegation ever assembled from one synagogue to the AIPAC conference in Washington in 2008, 2009, 2010, 2011, and 2012 with numbers ranging from 230-300 delegates. Wolpe also traveled to Haiti to help his friend Mitch Albom(Tuesdays with Morrie) rebuild an orphanage.[8]

On Passover 2001, Wolpe told his congregation that "the way the Bible describes the Exodus is not the way it happened, if it happened at all." Casting doubt on the historicity of the Exodus during the holiday that commemorates it brought condemnation from congregants and several rabbis (especially Orthodox Rabbis). The ensuing theological debate included whole issues of Jewish newspapers such as the Jewish Journal in Los Angeles and editorials in The Jerusalem Post, as well as an article in the Los Angeles Times. Critics asserted that Wolpe was attacking Jewish oral history, the significance of Passover and even the First Commandment.[citation needed] Wolpe asserted that he was arguing that the historicity of the events should not matter, since he believes faith is not determined by the same criteria as empirical truth. Wolpe argues that his views are based on the fact that no archeological digs have produced evidence of the Jews wandering the Sinai Desert for forty years, and that excavations in Israel consistently show settlement patterns at variance with the Biblical account of a sudden influx of Jews from Egypt.

In March 2010, Wolpe expounded on his views saying that it was possible that a small group of people left Egypt, came to Canaan, and influenced the native Canaanites with their traditions. He added that the controversy of 2001 stemmed from the fact that Conservative Jewish congregations have been slow to accept and embrace biblical criticism. Conservative rabbis, on the other hand, are taught biblical criticism in rabbinical school.[9]

On November 10, 2005, Rabbi Wolpe addressed the Jewish Theological Seminary and proposed that the name of Conservative Judaism be changed to "Covenantal Judaism," to better encompass the view that rabbinic law is both binding and evolving.

Why Faith Matters (2009) ISBN 0061633356, Rabbi Wolpe blends the powerful personal story of his struggles with his own faith with a poignant response to the new atheists that reveals just how important faith in modern society.

David: The Divided Heart (2014) ISBN 978-0300188783. Of all the figures in the Bible, David arguably stands out as the most perplexing and enigmatic. He was many things: a warrior who subdued Goliath and the Philistines; a king who united a nation; a poet who created beautiful, sensitive verse; a loyal servant of God who proposed the great Temple and founded the Messianic line; a schemer, deceiver, and adulterer who freely indulged his very human appetites.